Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026888/cv2246sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026888/cv2246Isup2.hkl |
CCDC reference: 654883
The title compound was synthesized with a yield of 75% according to the method reported in Author? (1989). The compound was purified by recrystallization from ethanol. The crystal was grown in acetone:toluene [50:50] solvent by the slow evaporation technique (m.p.:368–373 K). Analysis for C21H22O5: Found (Calculated): C: 71.20 (71.17%); H: 6.18 (6.22%).
The H atoms were included in calculated positions (C—H 0.95–0.98 Å) and refined in riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C).
The title compound, C21H22O5, 1,5-bis(3,4-dimethoxyphenyl) penta-1,4-dien-3-one, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely related to the title compound is Curcumin, (1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione), which is the main constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, antibacterial, antioxidant, antihepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is nontoxic at high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004).
Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004) as well as related crystal and molecular structural studies of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006). In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound C21H22O5.
For biological activity of the title compound and curcumin, see: Reksohadiprodjo et al. (2004). For hydrogen-bonding interactions and related structures, see: Girija et al. (2004) and Butcher et al. (2006). For related literature, see: Author? (1989).
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C21H22O5 | F(000) = 1504 |
Mr = 354.39 | Dx = 1.297 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.1646 (13) Å | Cell parameters from 7695 reflections |
b = 7.7488 (5) Å | θ = 2.8–29.6° |
c = 24.8495 (17) Å | µ = 0.09 mm−1 |
β = 100.414 (1)° | T = 103 K |
V = 3629.4 (4) Å3 | Prism, colourless |
Z = 8 | 0.56 × 0.35 × 0.24 mm |
CCD area-detector diffractometer | 10146 independent reflections |
Radiation source: fine-focus sealed tube | 8569 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 29.7°, θmin = 1.7° |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | h = −26→26 |
Tmin = 0.950, Tmax = 0.988 | k = −10→10 |
40342 measured reflections | l = −33→34 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.9436P] where P = (Fo2 + 2Fc2)/3 |
10146 reflections | (Δ/σ)max = 0.002 |
477 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C21H22O5 | V = 3629.4 (4) Å3 |
Mr = 354.39 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.1646 (13) Å | µ = 0.09 mm−1 |
b = 7.7488 (5) Å | T = 103 K |
c = 24.8495 (17) Å | 0.56 × 0.35 × 0.24 mm |
β = 100.414 (1)° |
CCD area-detector diffractometer | 10146 independent reflections |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | 8569 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.988 | Rint = 0.027 |
40342 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.34 e Å−3 |
10146 reflections | Δρmin = −0.29 e Å−3 |
477 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.70296 (4) | 0.41530 (11) | 0.25313 (3) | 0.02419 (17) | |
O2A | 0.70709 (4) | 0.51375 (11) | 0.35211 (3) | 0.02445 (17) | |
O3A | 0.35878 (4) | 0.45882 (11) | 0.07001 (3) | 0.02442 (17) | |
O4A | 0.07684 (4) | 0.86400 (10) | 0.20454 (3) | 0.02421 (17) | |
O5A | −0.02272 (4) | 0.63640 (10) | 0.18184 (3) | 0.02352 (16) | |
O1B | 0.96885 (4) | 0.17449 (11) | 0.03878 (3) | 0.02650 (17) | |
O2B | 0.93567 (4) | 0.07348 (11) | 0.13096 (3) | 0.02318 (16) | |
O3B | 0.55536 (4) | 0.26262 (11) | 0.10438 (3) | 0.02574 (17) | |
O4B | 0.22391 (4) | 0.28208 (11) | −0.09563 (3) | 0.02277 (16) | |
O5B | 0.23280 (4) | 0.19771 (11) | −0.19409 (3) | 0.02292 (16) | |
C1A | 0.51544 (5) | 0.55102 (12) | 0.24296 (4) | 0.01736 (18) | |
C2A | 0.57740 (5) | 0.48719 (13) | 0.22675 (4) | 0.01750 (18) | |
H2AA | 0.5761 | 0.4518 | 0.1900 | 0.021* | |
C3A | 0.63995 (5) | 0.47606 (13) | 0.26423 (4) | 0.01795 (19) | |
C4A | 0.64228 (5) | 0.52836 (13) | 0.31906 (4) | 0.01887 (19) | |
C5A | 0.58134 (6) | 0.58896 (13) | 0.33525 (4) | 0.0203 (2) | |
H5AA | 0.5824 | 0.6228 | 0.3721 | 0.024* | |
C6A | 0.51839 (5) | 0.60011 (13) | 0.29714 (4) | 0.01938 (19) | |
H6AA | 0.4767 | 0.6420 | 0.3084 | 0.023* | |
C7A | 0.70226 (6) | 0.35031 (15) | 0.19927 (4) | 0.0241 (2) | |
H7AA | 0.7499 | 0.3101 | 0.1962 | 0.036* | |
H7AB | 0.6877 | 0.4422 | 0.1725 | 0.036* | |
H7AC | 0.6687 | 0.2540 | 0.1921 | 0.036* | |
C8A | 0.70952 (7) | 0.54299 (16) | 0.40909 (5) | 0.0300 (3) | |
H8AA | 0.7580 | 0.5249 | 0.4289 | 0.045* | |
H8AB | 0.6774 | 0.4624 | 0.4228 | 0.045* | |
H8AC | 0.6948 | 0.6618 | 0.4148 | 0.045* | |
C9A | 0.44789 (5) | 0.56426 (13) | 0.20514 (4) | 0.01823 (19) | |
H9AA | 0.4086 | 0.6059 | 0.2198 | 0.022* | |
C10A | 0.43560 (5) | 0.52354 (13) | 0.15173 (4) | 0.01880 (19) | |
H10A | 0.4753 | 0.4958 | 0.1354 | 0.023* | |
C11A | 0.36532 (5) | 0.51882 (13) | 0.11681 (4) | 0.01848 (19) | |
C12A | 0.30154 (5) | 0.57637 (13) | 0.13791 (4) | 0.01858 (19) | |
H12A | 0.3056 | 0.6593 | 0.1665 | 0.022* | |
C13A | 0.23810 (5) | 0.50987 (13) | 0.11618 (4) | 0.01900 (19) | |
H13A | 0.2375 | 0.4299 | 0.0871 | 0.023* | |
C14A | 0.16988 (5) | 0.54584 (13) | 0.13193 (4) | 0.01782 (19) | |
C15A | 0.15812 (5) | 0.69605 (13) | 0.16107 (4) | 0.01781 (19) | |
H15A | 0.1948 | 0.7794 | 0.1698 | 0.021* | |
C16A | 0.09345 (5) | 0.72227 (13) | 0.17689 (4) | 0.01791 (19) | |
C17A | 0.03876 (5) | 0.59741 (13) | 0.16468 (4) | 0.01875 (19) | |
C18A | 0.05038 (5) | 0.44979 (14) | 0.13599 (4) | 0.0204 (2) | |
H18A | 0.0143 | 0.3649 | 0.1279 | 0.024* | |
C19A | 0.11532 (5) | 0.42641 (14) | 0.11907 (4) | 0.0204 (2) | |
H19A | 0.1224 | 0.3269 | 0.0984 | 0.025* | |
C20A | 0.11770 (6) | 1.01596 (15) | 0.20083 (6) | 0.0313 (3) | |
H20A | 0.0951 | 1.1144 | 0.2156 | 0.047* | |
H20B | 0.1204 | 1.0380 | 0.1624 | 0.047* | |
H20C | 0.1656 | 0.9999 | 0.2219 | 0.047* | |
C21A | −0.08162 (6) | 0.52357 (15) | 0.16435 (5) | 0.0269 (2) | |
H21A | −0.1246 | 0.5741 | 0.1739 | 0.040* | |
H21B | −0.0723 | 0.4115 | 0.1825 | 0.040* | |
H21C | −0.0882 | 0.5079 | 0.1246 | 0.040* | |
C1B | 0.75664 (5) | 0.19846 (13) | 0.05722 (4) | 0.01803 (19) | |
C2B | 0.77562 (6) | 0.25613 (14) | 0.00882 (4) | 0.0209 (2) | |
H2BA | 0.7403 | 0.3014 | −0.0194 | 0.025* | |
C3B | 0.84584 (6) | 0.24834 (14) | 0.00126 (4) | 0.0225 (2) | |
H3BA | 0.8577 | 0.2864 | −0.0323 | 0.027* | |
C4B | 0.89870 (5) | 0.18555 (14) | 0.04228 (4) | 0.0205 (2) | |
C5B | 0.88064 (5) | 0.12898 (13) | 0.09200 (4) | 0.01874 (19) | |
C6B | 0.81052 (5) | 0.13416 (13) | 0.09856 (4) | 0.01809 (19) | |
H6BA | 0.7984 | 0.0934 | 0.1317 | 0.022* | |
C7B | 0.98831 (7) | 0.22779 (19) | −0.01151 (5) | 0.0341 (3) | |
H7BA | 1.0395 | 0.2129 | −0.0093 | 0.051* | |
H7BB | 0.9759 | 0.3496 | −0.0182 | 0.051* | |
H7BC | 0.9629 | 0.1575 | −0.0416 | 0.051* | |
C8B | 0.91785 (6) | 0.02067 (15) | 0.18211 (4) | 0.0234 (2) | |
H8BA | 0.9608 | −0.0180 | 0.2068 | 0.035* | |
H8BB | 0.8836 | −0.0743 | 0.1758 | 0.035* | |
H8BC | 0.8970 | 0.1182 | 0.1987 | 0.035* | |
C9B | 0.68407 (5) | 0.20273 (13) | 0.06781 (4) | 0.01842 (19) | |
H9BA | 0.6772 | 0.1543 | 0.1016 | 0.022* | |
C10B | 0.62599 (5) | 0.26665 (14) | 0.03565 (4) | 0.01972 (19) | |
H10B | 0.6289 | 0.3116 | 0.0006 | 0.024* | |
C11B | 0.55731 (5) | 0.26688 (13) | 0.05515 (4) | 0.01883 (19) | |
C12B | 0.49040 (5) | 0.27168 (14) | 0.01548 (4) | 0.0203 (2) | |
H12B | 0.4485 | 0.3035 | 0.0285 | 0.024* | |
C13B | 0.48442 (5) | 0.23422 (13) | −0.03785 (4) | 0.0198 (2) | |
H13B | 0.5272 | 0.2112 | −0.0507 | 0.024* | |
C14B | 0.41874 (5) | 0.22514 (13) | −0.07822 (4) | 0.01829 (19) | |
C15B | 0.35178 (5) | 0.26085 (13) | −0.06460 (4) | 0.01829 (19) | |
H15B | 0.3484 | 0.2924 | −0.0282 | 0.022* | |
C16B | 0.29111 (5) | 0.24990 (13) | −0.10418 (4) | 0.01745 (19) | |
C17B | 0.29605 (5) | 0.20299 (13) | −0.15844 (4) | 0.01816 (19) | |
C18B | 0.36156 (6) | 0.16712 (13) | −0.17167 (4) | 0.0200 (2) | |
H18B | 0.3650 | 0.1348 | −0.2080 | 0.024* | |
C19B | 0.42248 (5) | 0.17860 (14) | −0.13161 (4) | 0.0205 (2) | |
H19B | 0.4674 | 0.1542 | −0.1410 | 0.025* | |
C20B | 0.21431 (6) | 0.28988 (17) | −0.04009 (5) | 0.0278 (2) | |
H20D | 0.1639 | 0.3061 | −0.0390 | 0.042* | |
H20E | 0.2416 | 0.3868 | −0.0217 | 0.042* | |
H20F | 0.2309 | 0.1820 | −0.0215 | 0.042* | |
C21B | 0.23441 (6) | 0.13995 (15) | −0.24840 (4) | 0.0253 (2) | |
H21D | 0.1859 | 0.1326 | −0.2691 | 0.038* | |
H21E | 0.2567 | 0.0259 | −0.2470 | 0.038* | |
H21F | 0.2617 | 0.2217 | −0.2664 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0163 (3) | 0.0342 (4) | 0.0214 (4) | 0.0047 (3) | 0.0016 (3) | −0.0053 (3) |
O2A | 0.0222 (4) | 0.0294 (4) | 0.0191 (4) | 0.0030 (3) | −0.0033 (3) | −0.0023 (3) |
O3A | 0.0203 (4) | 0.0366 (4) | 0.0169 (3) | 0.0041 (3) | 0.0046 (3) | −0.0010 (3) |
O4A | 0.0183 (3) | 0.0207 (4) | 0.0351 (4) | −0.0012 (3) | 0.0089 (3) | −0.0060 (3) |
O5A | 0.0137 (3) | 0.0242 (4) | 0.0338 (4) | −0.0017 (3) | 0.0073 (3) | −0.0027 (3) |
O1B | 0.0181 (4) | 0.0362 (4) | 0.0271 (4) | −0.0012 (3) | 0.0092 (3) | −0.0004 (3) |
O2B | 0.0148 (3) | 0.0317 (4) | 0.0227 (4) | 0.0029 (3) | 0.0026 (3) | 0.0037 (3) |
O3B | 0.0219 (4) | 0.0383 (4) | 0.0172 (4) | 0.0051 (3) | 0.0040 (3) | 0.0003 (3) |
O4B | 0.0158 (3) | 0.0340 (4) | 0.0187 (3) | 0.0047 (3) | 0.0037 (3) | −0.0016 (3) |
O5B | 0.0203 (4) | 0.0321 (4) | 0.0153 (3) | −0.0008 (3) | 0.0004 (3) | −0.0028 (3) |
C1A | 0.0166 (4) | 0.0167 (4) | 0.0188 (4) | 0.0001 (3) | 0.0034 (3) | 0.0011 (3) |
C2A | 0.0176 (4) | 0.0192 (4) | 0.0158 (4) | 0.0001 (3) | 0.0033 (3) | 0.0003 (3) |
C3A | 0.0162 (4) | 0.0181 (4) | 0.0197 (5) | 0.0012 (3) | 0.0037 (4) | 0.0006 (4) |
C4A | 0.0201 (5) | 0.0173 (4) | 0.0178 (4) | −0.0005 (4) | 0.0000 (4) | 0.0013 (3) |
C5A | 0.0247 (5) | 0.0192 (4) | 0.0170 (4) | −0.0006 (4) | 0.0041 (4) | −0.0011 (4) |
C6A | 0.0203 (5) | 0.0191 (4) | 0.0199 (5) | 0.0007 (4) | 0.0067 (4) | 0.0000 (4) |
C7A | 0.0212 (5) | 0.0289 (5) | 0.0229 (5) | 0.0041 (4) | 0.0054 (4) | −0.0039 (4) |
C8A | 0.0350 (6) | 0.0329 (6) | 0.0187 (5) | 0.0019 (5) | −0.0041 (4) | −0.0009 (4) |
C9A | 0.0158 (4) | 0.0179 (4) | 0.0215 (5) | 0.0017 (3) | 0.0049 (4) | 0.0013 (4) |
C10A | 0.0145 (4) | 0.0220 (5) | 0.0204 (5) | 0.0029 (4) | 0.0046 (4) | 0.0011 (4) |
C11A | 0.0170 (4) | 0.0207 (4) | 0.0184 (4) | 0.0022 (4) | 0.0050 (4) | 0.0032 (4) |
C12A | 0.0172 (4) | 0.0218 (5) | 0.0173 (4) | 0.0036 (4) | 0.0045 (4) | 0.0013 (4) |
C13A | 0.0181 (4) | 0.0230 (5) | 0.0164 (4) | 0.0027 (4) | 0.0044 (3) | 0.0009 (4) |
C14A | 0.0152 (4) | 0.0227 (5) | 0.0156 (4) | 0.0019 (4) | 0.0027 (3) | 0.0027 (4) |
C15A | 0.0142 (4) | 0.0202 (4) | 0.0187 (4) | −0.0003 (3) | 0.0021 (3) | 0.0016 (4) |
C16A | 0.0158 (4) | 0.0189 (4) | 0.0188 (4) | 0.0010 (3) | 0.0027 (3) | 0.0005 (3) |
C17A | 0.0134 (4) | 0.0223 (5) | 0.0209 (5) | 0.0006 (3) | 0.0038 (3) | 0.0030 (4) |
C18A | 0.0167 (4) | 0.0216 (5) | 0.0222 (5) | −0.0025 (4) | 0.0018 (4) | −0.0001 (4) |
C19A | 0.0190 (5) | 0.0223 (5) | 0.0195 (5) | 0.0005 (4) | 0.0024 (4) | −0.0021 (4) |
C20A | 0.0262 (5) | 0.0203 (5) | 0.0491 (7) | −0.0033 (4) | 0.0111 (5) | −0.0044 (5) |
C21A | 0.0152 (4) | 0.0283 (5) | 0.0373 (6) | −0.0037 (4) | 0.0050 (4) | −0.0003 (5) |
C1B | 0.0166 (4) | 0.0194 (4) | 0.0179 (4) | 0.0002 (3) | 0.0026 (3) | −0.0019 (3) |
C2B | 0.0197 (5) | 0.0249 (5) | 0.0176 (5) | −0.0002 (4) | 0.0018 (4) | 0.0001 (4) |
C3B | 0.0234 (5) | 0.0272 (5) | 0.0181 (5) | −0.0021 (4) | 0.0065 (4) | −0.0006 (4) |
C4B | 0.0170 (4) | 0.0227 (5) | 0.0225 (5) | −0.0022 (4) | 0.0058 (4) | −0.0042 (4) |
C5B | 0.0167 (4) | 0.0192 (4) | 0.0197 (5) | 0.0008 (3) | 0.0018 (4) | −0.0015 (4) |
C6B | 0.0175 (4) | 0.0197 (4) | 0.0171 (4) | 0.0009 (3) | 0.0032 (3) | −0.0006 (3) |
C7B | 0.0270 (6) | 0.0455 (7) | 0.0339 (7) | −0.0015 (5) | 0.0167 (5) | 0.0033 (5) |
C8B | 0.0185 (5) | 0.0284 (5) | 0.0230 (5) | 0.0034 (4) | 0.0031 (4) | 0.0049 (4) |
C9B | 0.0182 (4) | 0.0204 (4) | 0.0169 (4) | 0.0007 (4) | 0.0039 (4) | −0.0006 (4) |
C10B | 0.0179 (4) | 0.0239 (5) | 0.0174 (4) | 0.0002 (4) | 0.0033 (4) | 0.0013 (4) |
C11B | 0.0174 (4) | 0.0207 (4) | 0.0183 (5) | 0.0025 (4) | 0.0029 (4) | 0.0002 (4) |
C12B | 0.0157 (4) | 0.0249 (5) | 0.0206 (5) | 0.0030 (4) | 0.0035 (4) | 0.0003 (4) |
C13B | 0.0156 (4) | 0.0229 (5) | 0.0214 (5) | 0.0016 (4) | 0.0048 (4) | −0.0006 (4) |
C14B | 0.0170 (4) | 0.0194 (4) | 0.0186 (5) | 0.0004 (3) | 0.0034 (4) | −0.0007 (4) |
C15B | 0.0180 (4) | 0.0214 (5) | 0.0155 (4) | 0.0018 (4) | 0.0031 (4) | −0.0009 (3) |
C16B | 0.0166 (4) | 0.0186 (4) | 0.0175 (4) | 0.0018 (3) | 0.0043 (4) | 0.0002 (3) |
C17B | 0.0191 (4) | 0.0186 (4) | 0.0161 (4) | −0.0013 (4) | 0.0015 (4) | 0.0005 (3) |
C18B | 0.0233 (5) | 0.0213 (5) | 0.0164 (4) | −0.0014 (4) | 0.0059 (4) | −0.0017 (4) |
C19B | 0.0181 (4) | 0.0239 (5) | 0.0207 (5) | −0.0003 (4) | 0.0067 (4) | −0.0021 (4) |
C20B | 0.0225 (5) | 0.0411 (6) | 0.0212 (5) | 0.0049 (5) | 0.0075 (4) | −0.0036 (5) |
C21B | 0.0302 (6) | 0.0287 (5) | 0.0156 (5) | −0.0008 (4) | 0.0005 (4) | −0.0035 (4) |
O1A—C3A | 1.3698 (12) | C18A—C19A | 1.3956 (15) |
O1A—C7A | 1.4277 (13) | C18A—H18A | 0.9500 |
O2A—C4A | 1.3642 (12) | C19A—H19A | 0.9500 |
O2A—C8A | 1.4265 (14) | C20A—H20A | 0.9800 |
O3A—C11A | 1.2375 (13) | C20A—H20B | 0.9800 |
O4A—C16A | 1.3633 (12) | C20A—H20C | 0.9800 |
O4A—C20A | 1.4262 (13) | C21A—H21A | 0.9800 |
O5A—C17A | 1.3574 (12) | C21A—H21B | 0.9800 |
O5A—C21A | 1.4319 (13) | C21A—H21C | 0.9800 |
O1B—C4B | 1.3654 (12) | C1B—C2B | 1.3917 (15) |
O1B—C7B | 1.4280 (14) | C1B—C6B | 1.4092 (13) |
O2B—C5B | 1.3657 (12) | C1B—C9B | 1.4619 (14) |
O2B—C8B | 1.4342 (13) | C2B—C3B | 1.3933 (15) |
O3B—C11B | 1.2310 (13) | C2B—H2BA | 0.9500 |
O4B—C16B | 1.3655 (12) | C3B—C4B | 1.3890 (15) |
O4B—C20B | 1.4261 (13) | C3B—H3BA | 0.9500 |
O5B—C17B | 1.3667 (12) | C4B—C5B | 1.4117 (15) |
O5B—C21B | 1.4273 (13) | C5B—C6B | 1.3833 (14) |
C1A—C6A | 1.3903 (14) | C6B—H6BA | 0.9500 |
C1A—C2A | 1.4105 (14) | C7B—H7BA | 0.9800 |
C1A—C9A | 1.4594 (13) | C7B—H7BB | 0.9800 |
C2A—C3A | 1.3815 (13) | C7B—H7BC | 0.9800 |
C2A—H2AA | 0.9500 | C8B—H8BA | 0.9800 |
C3A—C4A | 1.4142 (14) | C8B—H8BB | 0.9800 |
C4A—C5A | 1.3843 (15) | C8B—H8BC | 0.9800 |
C5A—C6A | 1.3952 (14) | C9B—C10B | 1.3420 (14) |
C5A—H5AA | 0.9500 | C9B—H9BA | 0.9500 |
C6A—H6AA | 0.9500 | C10B—C11B | 1.4824 (14) |
C7A—H7AA | 0.9800 | C10B—H10B | 0.9500 |
C7A—H7AB | 0.9800 | C11B—C12B | 1.4699 (14) |
C7A—H7AC | 0.9800 | C12B—C13B | 1.3411 (15) |
C8A—H8AA | 0.9800 | C12B—H12B | 0.9500 |
C8A—H8AB | 0.9800 | C13B—C14B | 1.4626 (14) |
C8A—H8AC | 0.9800 | C13B—H13B | 0.9500 |
C9A—C10A | 1.3429 (14) | C14B—C19B | 1.3893 (14) |
C9A—H9AA | 0.9500 | C14B—C15B | 1.4123 (14) |
C10A—C11A | 1.4649 (13) | C15B—C16B | 1.3833 (13) |
C10A—H10A | 0.9500 | C15B—H15B | 0.9500 |
C11A—C12A | 1.4832 (14) | C16B—C17B | 1.4159 (14) |
C12A—C13A | 1.3409 (14) | C17B—C18B | 1.3824 (14) |
C12A—H12A | 0.9500 | C18B—C19B | 1.3935 (14) |
C13A—C14A | 1.4578 (14) | C18B—H18B | 0.9500 |
C13A—H13A | 0.9500 | C19B—H19B | 0.9500 |
C14A—C19A | 1.3897 (14) | C20B—H20D | 0.9800 |
C14A—C15A | 1.4102 (14) | C20B—H20E | 0.9800 |
C15A—C16A | 1.3813 (14) | C20B—H20F | 0.9800 |
C15A—H15A | 0.9500 | C21B—H21D | 0.9800 |
C16A—C17A | 1.4184 (14) | C21B—H21E | 0.9800 |
C17A—C18A | 1.3870 (15) | C21B—H21F | 0.9800 |
C3A—O1A—C7A | 116.80 (8) | H21A—C21A—H21B | 109.5 |
C4A—O2A—C8A | 116.57 (9) | O5A—C21A—H21C | 109.5 |
C16A—O4A—C20A | 116.84 (9) | H21A—C21A—H21C | 109.5 |
C17A—O5A—C21A | 116.75 (9) | H21B—C21A—H21C | 109.5 |
C4B—O1B—C7B | 116.98 (9) | C2B—C1B—C6B | 118.16 (9) |
C5B—O2B—C8B | 116.16 (8) | C2B—C1B—C9B | 123.64 (9) |
C16B—O4B—C20B | 116.66 (8) | C6B—C1B—C9B | 118.19 (9) |
C17B—O5B—C21B | 117.00 (8) | C1B—C2B—C3B | 120.82 (10) |
C6A—C1A—C2A | 118.92 (9) | C1B—C2B—H2BA | 119.6 |
C6A—C1A—C9A | 118.71 (9) | C3B—C2B—H2BA | 119.6 |
C2A—C1A—C9A | 122.37 (9) | C4B—C3B—C2B | 120.69 (10) |
C3A—C2A—C1A | 120.14 (9) | C4B—C3B—H3BA | 119.7 |
C3A—C2A—H2AA | 119.9 | C2B—C3B—H3BA | 119.7 |
C1A—C2A—H2AA | 119.9 | O1B—C4B—C3B | 124.82 (10) |
O1A—C3A—C2A | 125.08 (9) | O1B—C4B—C5B | 115.87 (9) |
O1A—C3A—C4A | 114.65 (8) | C3B—C4B—C5B | 119.30 (9) |
C2A—C3A—C4A | 120.27 (9) | O2B—C5B—C6B | 124.61 (9) |
O2A—C4A—C5A | 125.26 (9) | O2B—C5B—C4B | 115.98 (9) |
O2A—C4A—C3A | 115.02 (9) | C6B—C5B—C4B | 119.42 (9) |
C5A—C4A—C3A | 119.71 (9) | C5B—C6B—C1B | 121.59 (10) |
C4A—C5A—C6A | 119.69 (9) | C5B—C6B—H6BA | 119.2 |
C4A—C5A—H5AA | 120.2 | C1B—C6B—H6BA | 119.2 |
C6A—C5A—H5AA | 120.2 | O1B—C7B—H7BA | 109.5 |
C1A—C6A—C5A | 121.27 (9) | O1B—C7B—H7BB | 109.5 |
C1A—C6A—H6AA | 119.4 | H7BA—C7B—H7BB | 109.5 |
C5A—C6A—H6AA | 119.4 | O1B—C7B—H7BC | 109.5 |
O1A—C7A—H7AA | 109.5 | H7BA—C7B—H7BC | 109.5 |
O1A—C7A—H7AB | 109.5 | H7BB—C7B—H7BC | 109.5 |
H7AA—C7A—H7AB | 109.5 | O2B—C8B—H8BA | 109.5 |
O1A—C7A—H7AC | 109.5 | O2B—C8B—H8BB | 109.5 |
H7AA—C7A—H7AC | 109.5 | H8BA—C8B—H8BB | 109.5 |
H7AB—C7A—H7AC | 109.5 | O2B—C8B—H8BC | 109.5 |
O2A—C8A—H8AA | 109.5 | H8BA—C8B—H8BC | 109.5 |
O2A—C8A—H8AB | 109.5 | H8BB—C8B—H8BC | 109.5 |
H8AA—C8A—H8AB | 109.5 | C10B—C9B—C1B | 127.94 (10) |
O2A—C8A—H8AC | 109.5 | C10B—C9B—H9BA | 116.0 |
H8AA—C8A—H8AC | 109.5 | C1B—C9B—H9BA | 116.0 |
H8AB—C8A—H8AC | 109.5 | C9B—C10B—C11B | 119.72 (9) |
C10A—C9A—C1A | 126.63 (9) | C9B—C10B—H10B | 120.1 |
C10A—C9A—H9AA | 116.7 | C11B—C10B—H10B | 120.1 |
C1A—C9A—H9AA | 116.7 | O3B—C11B—C12B | 119.19 (9) |
C9A—C10A—C11A | 124.72 (9) | O3B—C11B—C10B | 120.86 (9) |
C9A—C10A—H10A | 117.6 | C12B—C11B—C10B | 119.96 (9) |
C11A—C10A—H10A | 117.6 | C13B—C12B—C11B | 124.44 (9) |
O3A—C11A—C10A | 119.48 (9) | C13B—C12B—H12B | 117.8 |
O3A—C11A—C12A | 119.69 (9) | C11B—C12B—H12B | 117.8 |
C10A—C11A—C12A | 120.75 (9) | C12B—C13B—C14B | 126.68 (10) |
C13A—C12A—C11A | 119.16 (9) | C12B—C13B—H13B | 116.7 |
C13A—C12A—H12A | 120.4 | C14B—C13B—H13B | 116.7 |
C11A—C12A—H12A | 120.4 | C19B—C14B—C15B | 119.05 (9) |
C12A—C13A—C14A | 127.61 (10) | C19B—C14B—C13B | 118.75 (9) |
C12A—C13A—H13A | 116.2 | C15B—C14B—C13B | 122.20 (9) |
C14A—C13A—H13A | 116.2 | C16B—C15B—C14B | 120.08 (9) |
C19A—C14A—C15A | 118.97 (9) | C16B—C15B—H15B | 120.0 |
C19A—C14A—C13A | 119.01 (9) | C14B—C15B—H15B | 120.0 |
C15A—C14A—C13A | 122.00 (9) | O4B—C16B—C15B | 124.98 (9) |
C16A—C15A—C14A | 120.15 (9) | O4B—C16B—C17B | 114.99 (8) |
C16A—C15A—H15A | 119.9 | C15B—C16B—C17B | 120.03 (9) |
C14A—C15A—H15A | 119.9 | O5B—C17B—C18B | 125.24 (9) |
O4A—C16A—C15A | 124.41 (9) | O5B—C17B—C16B | 114.89 (9) |
O4A—C16A—C17A | 115.24 (9) | C18B—C17B—C16B | 119.88 (9) |
C15A—C16A—C17A | 120.35 (9) | C17B—C18B—C19B | 119.79 (9) |
O5A—C17A—C18A | 125.04 (9) | C17B—C18B—H18B | 120.1 |
O5A—C17A—C16A | 115.52 (9) | C19B—C18B—H18B | 120.1 |
C18A—C17A—C16A | 119.43 (9) | C14B—C19B—C18B | 121.17 (9) |
C17A—C18A—C19A | 119.79 (9) | C14B—C19B—H19B | 119.4 |
C17A—C18A—H18A | 120.1 | C18B—C19B—H19B | 119.4 |
C19A—C18A—H18A | 120.1 | O4B—C20B—H20D | 109.5 |
C14A—C19A—C18A | 121.27 (10) | O4B—C20B—H20E | 109.5 |
C14A—C19A—H19A | 119.4 | H20D—C20B—H20E | 109.5 |
C18A—C19A—H19A | 119.4 | O4B—C20B—H20F | 109.5 |
O4A—C20A—H20A | 109.5 | H20D—C20B—H20F | 109.5 |
O4A—C20A—H20B | 109.5 | H20E—C20B—H20F | 109.5 |
H20A—C20A—H20B | 109.5 | O5B—C21B—H21D | 109.5 |
O4A—C20A—H20C | 109.5 | O5B—C21B—H21E | 109.5 |
H20A—C20A—H20C | 109.5 | H21D—C21B—H21E | 109.5 |
H20B—C20A—H20C | 109.5 | O5B—C21B—H21F | 109.5 |
O5A—C21A—H21A | 109.5 | H21D—C21B—H21F | 109.5 |
O5A—C21A—H21B | 109.5 | H21E—C21B—H21F | 109.5 |
C6A—C1A—C2A—C3A | −0.78 (14) | C6B—C1B—C2B—C3B | 0.80 (15) |
C9A—C1A—C2A—C3A | −179.53 (9) | C9B—C1B—C2B—C3B | −179.93 (10) |
C7A—O1A—C3A—C2A | −3.51 (15) | C1B—C2B—C3B—C4B | −1.13 (16) |
C7A—O1A—C3A—C4A | 176.01 (9) | C7B—O1B—C4B—C3B | −1.64 (16) |
C1A—C2A—C3A—O1A | 179.57 (9) | C7B—O1B—C4B—C5B | 178.82 (10) |
C1A—C2A—C3A—C4A | 0.06 (15) | C2B—C3B—C4B—O1B | −179.40 (10) |
C8A—O2A—C4A—C5A | 8.28 (15) | C2B—C3B—C4B—C5B | 0.12 (16) |
C8A—O2A—C4A—C3A | −171.83 (9) | C8B—O2B—C5B—C6B | −1.15 (15) |
O1A—C3A—C4A—O2A | 1.32 (13) | C8B—O2B—C5B—C4B | 178.23 (9) |
C2A—C3A—C4A—O2A | −179.13 (9) | O1B—C4B—C5B—O2B | 1.32 (14) |
O1A—C3A—C4A—C5A | −178.78 (9) | C3B—C4B—C5B—O2B | −178.24 (9) |
C2A—C3A—C4A—C5A | 0.77 (15) | O1B—C4B—C5B—C6B | −179.26 (9) |
O2A—C4A—C5A—C6A | 179.01 (9) | C3B—C4B—C5B—C6B | 1.18 (15) |
C3A—C4A—C5A—C6A | −0.88 (15) | O2B—C5B—C6B—C1B | 177.85 (9) |
C2A—C1A—C6A—C5A | 0.67 (15) | C4B—C5B—C6B—C1B | −1.51 (15) |
C9A—C1A—C6A—C5A | 179.47 (9) | C2B—C1B—C6B—C5B | 0.52 (15) |
C4A—C5A—C6A—C1A | 0.16 (15) | C9B—C1B—C6B—C5B | −178.78 (9) |
C6A—C1A—C9A—C10A | 179.67 (10) | C2B—C1B—C9B—C10B | −3.14 (17) |
C2A—C1A—C9A—C10A | −1.58 (16) | C6B—C1B—C9B—C10B | 176.12 (10) |
C1A—C9A—C10A—C11A | 172.18 (9) | C1B—C9B—C10B—C11B | −176.83 (9) |
C9A—C10A—C11A—O3A | −170.90 (10) | C9B—C10B—C11B—O3B | 23.27 (15) |
C9A—C10A—C11A—C12A | 5.81 (16) | C9B—C10B—C11B—C12B | −156.53 (10) |
O3A—C11A—C12A—C13A | 23.71 (15) | O3B—C11B—C12B—C13B | −162.80 (11) |
C10A—C11A—C12A—C13A | −153.00 (10) | C10B—C11B—C12B—C13B | 17.01 (16) |
C11A—C12A—C13A—C14A | 178.36 (9) | C11B—C12B—C13B—C14B | 175.38 (10) |
C12A—C13A—C14A—C19A | −158.01 (11) | C12B—C13B—C14B—C19B | −177.88 (11) |
C12A—C13A—C14A—C15A | 20.32 (16) | C12B—C13B—C14B—C15B | 1.64 (17) |
C19A—C14A—C15A—C16A | 0.62 (14) | C19B—C14B—C15B—C16B | −0.23 (15) |
C13A—C14A—C15A—C16A | −177.70 (9) | C13B—C14B—C15B—C16B | −179.76 (9) |
C20A—O4A—C16A—C15A | 21.79 (15) | C20B—O4B—C16B—C15B | −14.48 (15) |
C20A—O4A—C16A—C17A | −158.30 (10) | C20B—O4B—C16B—C17B | 165.79 (9) |
C14A—C15A—C16A—O4A | −179.19 (9) | C14B—C15B—C16B—O4B | −179.77 (9) |
C14A—C15A—C16A—C17A | 0.91 (15) | C14B—C15B—C16B—C17B | −0.05 (15) |
C21A—O5A—C17A—C18A | −6.10 (15) | C21B—O5B—C17B—C18B | 4.18 (15) |
C21A—O5A—C17A—C16A | 172.56 (9) | C21B—O5B—C17B—C16B | −175.94 (9) |
O4A—C16A—C17A—O5A | 0.40 (13) | O4B—C16B—C17B—O5B | 0.25 (13) |
C15A—C16A—C17A—O5A | −179.69 (9) | C15B—C16B—C17B—O5B | −179.49 (9) |
O4A—C16A—C17A—C18A | 179.14 (9) | O4B—C16B—C17B—C18B | −179.85 (9) |
C15A—C16A—C17A—C18A | −0.94 (15) | C15B—C16B—C17B—C18B | 0.41 (15) |
O5A—C17A—C18A—C19A | 178.06 (10) | O5B—C17B—C18B—C19B | 179.41 (10) |
C16A—C17A—C18A—C19A | −0.56 (15) | C16B—C17B—C18B—C19B | −0.48 (15) |
C15A—C14A—C19A—C18A | −2.16 (15) | C15B—C14B—C19B—C18B | 0.16 (16) |
C13A—C14A—C19A—C18A | 176.22 (9) | C13B—C14B—C19B—C18B | 179.70 (9) |
C17A—C18A—C19A—C14A | 2.13 (16) | C17B—C18B—C19B—C14B | 0.20 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6AA···O3Bi | 0.95 | 2.54 | 3.2898 (13) | 137 |
C8A—H8AC···O3Ai | 0.98 | 2.58 | 3.5513 (15) | 173 |
C20A—H20C···O1Ai | 0.98 | 2.57 | 3.5085 (15) | 161 |
C8B—H8BA···O4Aii | 0.98 | 2.41 | 3.2334 (13) | 141 |
C8B—H8BB···O5Biii | 0.98 | 2.54 | 3.4056 (14) | 147 |
C10B—H10B···O3Aiv | 0.95 | 2.54 | 3.4325 (13) | 157 |
C12B—H12B···O3A | 0.95 | 2.47 | 3.3968 (13) | 164 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y−1, z; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H22O5 |
Mr | 354.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 103 |
a, b, c (Å) | 19.1646 (13), 7.7488 (5), 24.8495 (17) |
β (°) | 100.414 (1) |
V (Å3) | 3629.4 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.56 × 0.35 × 0.24 |
Data collection | |
Diffractometer | CCD area-detector |
Absorption correction | Multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.950, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40342, 10146, 8569 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.697 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.114, 1.03 |
No. of reflections | 10146 |
No. of parameters | 477 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.29 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6AA···O3Bi | 0.95 | 2.54 | 3.2898 (13) | 136.5 |
C8A—H8AC···O3Ai | 0.98 | 2.58 | 3.5513 (15) | 173.1 |
C20A—H20C···O1Ai | 0.98 | 2.57 | 3.5085 (15) | 161.0 |
C8B—H8BA···O4Aii | 0.98 | 2.41 | 3.2334 (13) | 140.8 |
C8B—H8BB···O5Biii | 0.98 | 2.54 | 3.4056 (14) | 147.0 |
C10B—H10B···O3Aiv | 0.95 | 2.54 | 3.4325 (13) | 156.8 |
C12B—H12B···O3A | 0.95 | 2.47 | 3.3968 (13) | 164.2 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y−1, z; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z. |
The title compound, C21H22O5, 1,5-bis(3,4-dimethoxyphenyl) penta-1,4-dien-3-one, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely related to the title compound is Curcumin, (1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione), which is the main constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, antibacterial, antioxidant, antihepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is nontoxic at high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004).
Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004) as well as related crystal and molecular structural studies of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006). In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound C21H22O5.